Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 4-Iodo-1-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)-1H-pyrazole | HCID 59341852 | — |
| Reactant | HCID 86722831 | HCID 86722831 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86722833 | HCID 86722833 | 50.9% |
Reaction Steps
To a solution of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-3-vinyl-1H-pyrazolo[4,3-c]pyridine (0.1 mmol) in DMF (0.5 mL) was added 4-iodo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1H-pyrazole (44 mg, 0.14 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (7.5 mg, 0.0092 mmol), and water (0.05 mL). The mixture was degassed and sealed. It was stirred at 95° C. for 3 h. After cooling the solid was filtered off, washed with acetonitrile. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (32 mg). LCMS (M+H)+=628.2/630.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09266892B2 |
|---|
| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-23cd000d3ec2443cbe1fe8b18d1a8a10 |
|---|
| Source note | uspto-grants-2016_02 |
|---|
